Islamorada Waterfront Homes on the Bay / Gulf Side of the Island For Sale

Absolute showstopper with 150 of frontage overlooking some of the most pristine bay waters the Keys has to offer. Complete nut and bolt renovation with no corners cut. Deep water dockage for almost any size boat and access through Channel 5 to hit the ocean. The upstairs main living area offers 3 bedrooms/2 bathrooms, high-end kitchen appliances, and turquoise water views from almost every room. The downstairs separate guest quarters offers 1 bedroom/1 bathroom, living room, and kitchen. Pool permit in place or take a dip in the bay. This ones special, so dont miss the opportunity to be one of the cool kids.

Are you tired of waiting for Uber? Dont want to risk a DUI? Make this your bayfront estate and enjoy all that Islamorada has to offer. Just steps from MEAT, Shima and Marker 88 restaurants and just down the street from City Hall Cafe! Fully fenced for privacy, this property offers breathtaking bay views and an irreplaceable tiki at the end of the dock. You will make this your daily sunset viewing platform! Upstairs you will find a large open living area with sliding glass doors to the spacious screened terrace. In addition there are 3 bedrooms and 2 baths. From the terrace there are stairs to the pool and then the backyard, beach and dock. The ground level includes 2 bedrooms and bath plus an open living area. You will fall in love with this property and want to make it your Keys retreat or an investment opportunity to rent when you are not using it.

Timeless Waterfront Charm in Venetian Shores, Islamorada - Indulge in classic charm with this meticulously positioned waterfront residence in sought-after Venetian Shores. A dream come true for those who appreciate spectacular sunsets and unparalleled boating opportunities in the Florida Keys. Step into the gracious embrace of a bygone era in this residence poised directly on Snake Creek, the gateway to the Atlantic Ocean and Florida Bay, with prime fishing, diving, and waterfront dining just minutes away by boat. A celebration of classic waterfront living, the homes first floor unfolds with a spacious split plan, showcasing a large living room with a dining area, a family/game room blessed with water views on three sides, a water-view kitchen, and a central sunset-view screen porch. Three bedrooms, including two master suites--one featuring a private waterfront porch--and three full baths (two en suite), harmoniously combine casual refinement and comfort. Ascend a spiral staircase to the crown jewel--a top floor with panoramic water views, private balconies, and limitless possibilities. This space transforms into a fourth bedroom suite, a guest efficiency, or the grandkids playhouse, complete with a kitchenette, dining area, seating space, beds/bunk space, a full bath, and two closets. Moor your boat in the protected cut-in boat slip with davits. Delight in the waterside deck and Tiki hut, ideal for fishing or grilling, all while enjoying passing boats, dolphins, and sea life. Additional amenities include an outdoor shower, two carports, a storage/tackle room, covered seating and an elevator lift to the main floor. Recent upgrades include new storm shutters throughout and new impact windows to fortify the stairway tower. These enhancements add to the aesthetic appeal and are also crucial for windstorm insurance. This waterfront haven isnt just a residence - its a lifestyle. Seize this once-in-a-generation opportunity to make this dream lifestyle your own.

Welcome to your dream retreat on the bay in Venetian Shores - the Upper Keys favorite boating neighborhood! Boaters of all kinds will love the immediate bay access and lightning-quick ocean access via Snake Creek. With breathtaking views of the Florida Bay, and a sparkling pool, its the perfect place for relaxing and soaking in the sunshine. This stunning three-bedroom, two-bath beach has undergone a massive and stylish recent remodel. Youll love the timeless, modern coastal touches including the stunning new flooring! Vaulted ceilings and huge impact windows let the sunshine in. The homes open-concept design showcases panoramic bay views from almost every room. Each bedroom offers comfort and tranquility, with the master suite enjoying its own serene water views. Nestled on a dead-end street with only 12 homes, youll enjoy privacy galore. Keep a boat on the floating dock behind the house or in your boat slip just steps away, providing easy access to the crystal-clear waters of the Florida Keys. Whether youre looking for a peaceful escape or an active waterfront lifestyle, this property has it all--privacy, luxury, and unparalleled access to the best of Islamorada. Dont miss this rare opportunity to own a piece of paradise! Metal roof, impact windows and doors & artificial turf make maintenance a breeze. Electric fence. Boats to 40 and lifts allowed!

This exceptional Port Antigua residence, located on a tranquil cul-de-sac, boasts over 220 feet of concrete dockage including two boat lifts and a davit. As you enter through the exquisite hand-carved mahogany doors, youre greeted by a welcoming foyer with sliding glass doors that open to the pool and dock area. The elegant, curved staircase ascends to the main living area, featuring a spacious open-concept layout and a gourmet kitchen equipped with stainless steel appliances. The living side of the house includes two bedrooms, two bathrooms, and a laundry room, while a raised walkway leads to a secluded primary suite with a luxurious bathroom and an expansive dream closet. For those seeking sun and relaxation, the pool and hot tub provide the perfect retreat, complemented by a travertine pool deck and a brick-paved outdoor bar area, complete with a DCS grill and side burner. This shaded oasis is ideal for crafting tropical drinks and grilling your daily catch. Adjacent to the bar is a convenient pool cabana with a full bathroom. When its time to unwind indoors, head to the third floor, where a theater and game room await, complete with a wet bar and a popcorn machine. Two stunning stained glass windows depicting sea life add a unique touch, reminding you of the adventures that await on the water. The third floor also features a bedroom and a half-bath, along with an open lanai offering glimpses of the Atlantic. The expansive dock includes two gazebos--one for relaxation and the other for fish cleaning--along with a davit and two boat lifts, accommodating 20,000 lbs. and 12,000 lbs. Ample space between the lifts ensures room for your cruising yacht. This home is truly a unique gem in Port Antigua. Dont miss the opportunity to make it yours.

Discover coastal luxury in this stunning 4-bedroom, 4-bathroom bayside paradise. With 4,144 square feet of luxurious living space, this home offers breathtaking sunset views and direct access to the sparkling waters of the Florida Keys. Indulge in spacious, open-concept living areas, perfect for entertaining guests. Retreat to one of two primary suites, each featuring a large walk-in closet and private en-suite bathroom. Ascend to the rooftop deck and be rewarded with unobstructed, open-water bay views. The property features a separate living space, ideal for in-laws or guests, offering privacy and independence. The modern kitchen boasts sleek stainless steel appliances, double oven, gas appliances and ample counter space, perfect for culinary enthusiasts. The homes durable construction, including CBS, metal roof, and impact-resistant windows and doors, ensures peace of mind. For added security and privacy, the property is fully fenced and features an electric gate. Enjoy panoramic water views and unforgettable sunsets from your private oasis. With large boat dockage, youll have plenty of room for multiple boats, jet skis and easy access to the open water for boating, fishing, and other water activities. This completely updated home offers the ultimate experience in comfort and convenience. Whether youre seeking a serene retreat or an active water lovers paradise, this home has it all. Dont miss this opportunity to own a piece of paradise.

This remarkable 32,000 sq ft lot on the Florida Bay is a true paradise for anyone seeking a waterfront lifestyle in the heart of Islamorada, specifically Upper Matecumbe. With expansive open water views, this property offers an idyllic setting to enjoy the natural beauty of the Florida Bay.One of the key highlights of the lot is its exceptional dockage, which has previously accommodated a 36-foot boat, making it perfect for boating enthusiasts. The dock can be expanded to suit your needs, providing ample space for additional vessels or watercraft. The property also offers plenty of room for a pool and garage, allowing for a customized design that maximizes the waterfront experience. Beautiful sunsets grace the horizon, casting vibrant colors across the water and clouds creating a tranquil atmosphere for evening relaxation.The lot is also a sanctuary for wildlife enthusiasts, with an abundance of aqatic species like fish, birds, manatees and a mulitude of different birds. Zoned as Residential Estate, this property allows for weekly rentals, presenting an opportunity for investment or personal use. Its a perfect canvas for your dream residence or vacation retreat.With easy access to the Atlantic Ocean and iconic spots like Alligator Reef, whether you prefer fishing, diving, or simply unwinding by the water, this lot is one of the best properties on the market. Embrace the ultimate Florida Keys lifestyle in this exceptional location, where every day feels like a vacation.Owner / Agent

Welcome to paradise at 117 Leoni Drive in the exclusive Venetian Shores neighborhood! This stunning 4,100 sq. ft., canal-front home offers bay and ocean access via snake creek, 70 feet of dockage, and luxurious living with 5 bedrooms and 6 bathrooms. Built with precision and modern style, this brand-new custom CBS residence boasts lush landscaping, a sparkling pool, and high-end finishes throughout.Step upstairs to find a tranquil master suite with an expansive walk-in closet, a beverage center, a large shower, and dual vanities. Three additional guest suites with private bathrooms, a spacious living area, a large laundry room, and a versatile bonus room complete the upper level, providing ample space for relaxation and recreation.On the main floor, the gourmet kitchen is a chefs dream, featuring top-of-the-line appliances, storage pantry, Taj Mahal quartzite countertops, a wine cooler, and custom cabinetry throughout. A private guest room with an ensuite bathroom is perfect for the friends and family to visit for a staycation. The open-concept main living area flows seamlessly into the outdoors where a full bath and outdoor kitchen await. Relax by the lounge pool, enjoy synthetic grass surroundings, and take advantage of the full dock.This canal-front oasis is a rare find in the coveted Upper Keys and offers the perfect blend of luxury, comfort, and convenience. Your slice of paradise awaits!

Come home to outstanding views with 109 feet of bay frontage in Lower Matecumbe Key. This cottage-style home combines all of the elements of Florida Keys charm with captivating open water views and is situated on 1.3 acres of land. Complete with three bedrooms and two bathrooms, this ground-level, and updated residence is the perfect place to entertain while basking in all of the beauty the Keys offers. Zoned residential estate, this income-producing home qualifies for weekly rentals, which provides ample opportunities for a discerning buyer.

STUNNING PANORAMIC BAY VIEWS, sunsets and unparalleled privacy. This once-in-a-lifetime bay front property offers 200 feet of shoreline on Florida Bay with spectacular views. The property encompasses 2 and 1/2 lots, totaling a stunning three-quarters of an acre. The meticulously landscaped grounds, tended to by a Florida Master Gardener, provide a lush backdrop to the spacious residence. Boaters will love having a flats boat right behind the house along with TWO slips in the private marina just 800 feet from the front door. Each slip accommodates a boat to 40 LOA. Lifts allowed. Youll have immediate bay access and quick ocean via Snake Creek. At the heart of the estate, a sprawling one-level residence provides effortless living and lots of room for friends and family. An elevator provides easy access for everyone. A soaring cathedral tongue-and-groove ceilings create an airy sense of space, while oversized windows frame panoramic bay views from every angle. The living, dining, and kitchen areas seamlessly blend together, providing the perfect backdrop for entertaining or simply enjoying quiet moments with loved ones. A spacious screened porch offers a second living and dining area overlooking the bay. The primary suite boasts more breathtaking bay views and offers a peaceful retreat at the end of each day. Across the home, a separate wing awaits, ideal for hosting friends and family. Here, a large office, a cozy family room, and two additional bedrooms with en-suite baths provide ample space for guests to feel right at home. Youll find 3,000sf +/- under AC along with many, many additional outdoor living spaces. Additional square footage includes a 562sf workout room and a 1500sf garage (huge!) with a workshop and golf cart garage. Youll have PLENTY of space for cars, hobbies and storage. Almost all of the windows are impact and a 2003 5V crimp Galvalume metal roof provides peace of mind. Sellers have Army Corps and DEP approval for 60 observation pier!

$400,000 PRICE REDUCTION !! ... Welcome to Serenity Cove, a remarkable, comfortably luxurious estate set along the shores of the Florida Bay. This custom-designed property, stretching from the highway to the bay is almost 1.75 acres. It is perfect for those who value peace, relaxation, and the simple joys of what the Florida Keys has to offer.This home offers four bedrooms and four bathrooms and 110 of dock with multiple slips accommodating up to a 45 boat with 5 draft and 16k lift. This home has been thoughtfully designed with tasteful moldings, and warm, inviting finishes. The kitchen, is equipped with top-tier appliances, custom cabinetry, and a roomy island - perfect for those who love to cook and entertain. It smoothly transitions into the formal dining room, making it an ideal space for both quiet family dinners and larger celebrations.The second-floor suite, with its spacious layout, welcoming fireplace, and private balcony, is the ultimate retreat. The en-suite bathroom, has a dual vanity, a claw-foot soaking tub, and a walk-in shower, guarantees moments of relaxation.The first floor offers a smart design with separate living areas and bedrooms. The 1st floor suite includes a steam shower and a reinforced safe room that doubles as a walk-in closet. The additional two bedrooms and a den with surround sound and a wet bar are comfortably located on the opposite side of the home.Enjoy quiet moments on the covered patio or engage in lively gatherings around the spacious poolside patio, which leads directly to the sandy beach for amazing sunsets. Here, youll find ample seating, a fire pit, a Boat House and steps leading to the basin for swimming and exploring the Bays unique ecosystem.Serenity Cove is comfortably tucked away from the hustle of US1, offering a sense of privacy and security, while maintaining easy access to schools, shopping, dining that make Islamorada so desirable.

An incomparable bayside Islamorada compound with an exempted deep-dredge boat basin, this enchanting property provides 100 of direct waterfront and .7 acres of professionally manicured mature grounds. Move-in ready 4-bedroom residence offered for only the second time in a generation also provides an opportunity to build a one-of-a-kind property in the coveted Plantation Beach estate area. Enter via a gated entrance with stately mature mahogany trees and towering palms to your own private retreat. The serene and private sanctuary includes a saltwater infinity pool, complete with a spa, heater, and chiller. With year-round direct sunset views, enjoy golden hour evenings lit with tiki torches and landscape lighting throughout. This two-story above-flood traditional keys home offers four bedrooms and three full baths, with an interior staircase that includes separate quarters and an extra kitchenette - an ideal layout for family living or hosting guests. Additional features include a whole house generator, a security system, a spacious garage, and dolphin swim-bys. The neighborhood offers a homeowners park with a boat ramp, beach, and picnic area. It is on a quiet street amongst prestigious estates in a most desirable Plantation Key neighborhood.

Welcome to Bahia Bonita! This ultra-private bayfront estate in the heart of downtown Islamorada offers the ultimate combination of expansive open water views from every room plus deep-water dockage. If you have been wishing for an exceptional piece of Florida Keys paradise where natural beauty and luxury living meet storm resiliency, this solidly constructed, sustainably designed home may exceed your expectations. Begin your day by stepping out of your primary suite to your bayfront terrace and into an incomparable, second floor Infinity Edge pool. In the evening, slide open the wall of glass on the top floor to experience the brilliance of Islamoradas famous sunsets from your great room, gourmet kitchen or outdoor decks. Feel like grilling? Just one step away is an outdoor kitchen with bay view seating and adjacent dining. For stargazing, venture up the spiral stairs to the rooftop deck for a breathtaking front row seat. Built from solid concrete to withstand sustained 200 mph winds, this home also includes accordion shutters over impact glass for the ultimate defense against the elements. Outside, enjoy 250+ linear feet of open water frontage and a 100 dock with commercial-grade piles, composite decking and two boat lifts fitted with hurricane and storm surge protection. This unparalleled storm resiliency is combined with modern sustainability features including a large cistern with state-of-the-art water purification system, a grid-tied solar array and integrated Tesla Power Walls eliminating the need for a generator. Other functional luxuries built into the home are an elevator, professional camera/security system, central wet-dry vacuum system, mature landscaping and an enormous three-car garage, complete with workshop and storage. This home also boasts marble floors throughout and a spectacular floating staircase.This luxurious yet practical island estate is also within walking distance of many of Islamoradas favorite dining spots. Call today!

This exquisite bayfront Islamorada property features a main home with four bedrooms, four full bathrooms, and two half bathrooms, along with a guest house offering two bedrooms and one bathroom. The kitchen features marble countertops, a gas range, and counter seating. With a separate dining area and 30 ft high ceilings in the great room, floor-to-ceiling windows offer breathtaking views of the bay waters and dynamic sunset skies. The infinity edge pool with a spa offers reflections of beautiful palms and exquisite landscaping. The outdoor cabana kitchen is perfect for al fresco dining, and the boat basin with dockage allows for easy access to the waters of Florida Bay. A whole-house generator ensures uninterrupted comfort and tiki torches light the backyard terraces. Dont miss the waterfalls cascading into the boat basin, creating a truly serene retreat.

Unravel your dreams through this gated Estate Residence encompassing entire peninsula with over 500feet of bayfront and protected crystal clear waters. This pristine private luxury resort style property and residence includes designs by DAsign Source and provides ultimate privacy while exposing the surrounding majestic waters. Avid boaters will appreciate this dockage for multiple large boats, plus onsite boat ramp Y private boat lift. Marked features of this Estate include professionally designed infinity pool & waterfalls, jacuzzi, and salt water pond overlooking the bay, manicured lawns with 28 zone irrigation, extensive tropical landscaping, paver brick driveway, detached 2 car garage plus additional undercover parking, separate multipurpose CBS building, expansive outdoor porches and entertainment areas, German inspired indoor & outdoor fireplace, stand alone carport with car washing facilities, full home generator, home security system, advanced stereo system for interior & exterior of home. This custom designed concrete Residence consists of two buildings attached by large open covered breezeway. Enter into the foyer leading to a grand interior living and entertaining area offering views in every direction, all of which lead out to expansive wrap around porches. Custom gourmet kitchen with dual refrigerator, dual dishwashers, dual ranges, all Viking appliances, wet bar with wine cooler, & multiple sinks. Private office, walkin pantry, & guest bath. The sleeping quarters located in separate building offers private third floor master suite & bath with steam shower, jacuzzi tub, dual sinks, & a dream walkin closet. Two additional guests rooms, bathroom & living area on main level. Additional ground level cabana bar, plus private guest suite. This grand Estate home was completely rebuilt in 2006 and 2009 with two separate buildings attached by exceptional breezeway and all overlooking the beautiful gulf front waters. So much more...call for full details.

Welcome to BAYVIEW HIDEAWAY, a stunning private mini-estate fully reimagined during a meticulous 2020-2021 renovation, where the owners spared no expense. This remarkable property boasts 435+/- of water frontage which includes 220+ of concrete dockage. The canal has accommodated vessels of over 80+ with direct ocean access via the impressive 65-foot-clearance Channel 5 Bridge. A rare opportunity for privacy or development is offered with 215+/- of waterfront on a separate, corner, bay-front buildable lot. This breathtaking retreat features six bedrooms, including two luxurious primary suites, four bathrooms, and a spacious three-story layout with panoramic open-water sunset views. The custom illuminated saltwater pool, built in 2021, is complete with a brand new chiller/heater, surrounded by elegant marble pavers and outdoor amenities designed for relaxation and entertainment. Nestled in Islamorada, one of the Florida Keys most sought-after locations, the 4,394-square-foot home offers water views from every room, private balconies, and soaring vaulted ceilings in the living areas and primary suites. A 33-foot vaulted staircase with skylights serves as the architectural centerpiece, featuring Turkish marble steps and sleek glass railings. At the heart of the home, the chefs kitchen impresses with premium Viking appliances and a striking Vetrazzo countertop. The outdoor space is equally captivating, with a covered entertainment area poolside, three boat lifts, gazebo, two pergolas, three-hole putting green, and outdoor shower. Additional luxuries include an elevator to all three floors, a hidden mirror-door closet in the primary suite and Italian marble accents in the primary bath. Combining unparalleled water access, modern luxury and Florida Keys charm, BAYVIEW HIDEAWAY offers a lifestyle of exceptional refinement. Located minutes from Islamoradas downtown shopping, Alligator Lighthouse, and sandbars, this private retreat is the ultimate gateway to paradise.